Trifluoroacetic acid → HCID 14955036, compound

HRID 1197828Notes

Reaction equation

HRID 1197828 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]=[CH:3][C:2]1=[O:7].[CH2:8]([N:15]([CH2:21]OC)[CH2:16][Si](C)(C)C)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:8]([N:15]1[CH2:21][C@H:4]2[CH2:5][CH2:6][O:1][C:2](=[O:7])[C@H:3]2[CH2:16]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 5206603393-45-1

Product 1

HCID 14955036HCID 14955036, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 5,6-dihydro-2H-pyran-2-one* (136 g, 1.39 mole) in dichloromethane (2 L) at -20° C. was added N-benzyl-N-(methoxymethyl)-N-trimethylsilylmethyl amine (80% pure) (D12, 450 g, 1.5 mole). To this solution was added trifluoroacetic acid in dichloromethane (140 ml, 1 molar solution) at -20° C. The reaction was then transferred at -20° C. under a small positive pressure of nitrogen via a double ended needle to a second flask on a water bath at 30° C. As the cold mixture warmed up an exothermic reaction occurred and the rate of addition was controlled to maintain gentle reflux. When addition was complete and the reaction had subsided the solution was allowed to stand at room temperature for 2 h. The reaction was then washed with saturated aqueous potassium carbonate solution, dried (Na2SO4) and concentrated in vacuo to a gum. Vacuum distillation afforded the title compound as a single main fraction b.p. 180°-190° C.0.5mmHg (D20, 180.9 g, 0.73 mole, 56%).

Workup

  1. customwas then transferred at -20° C. under a small positive pressure of nitrogen
  2. customat 30° C
  3. temperatureAs the cold mixture warmed up
  4. customan exothermic reaction
  5. additionthe rate of addition
  6. temperatureto maintain gentle reflux
  7. additionWhen addition
  8. washThe reaction was then washed with saturated aqueous potassium carbonate solution
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated in vacuo to a gum
  11. distillationVacuum distillation

Sources & evidence

ORD record
ord-61758ab460644e9f92e3127aaa9b30c5
Source dataset
uspto-grants-1994_01
Patent number
US05278170

Reaction notes

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